On why "fixing" iPhone's Exchange support shows that Apple is clueless about the enterprise

I upgraded to iPhone OS 3.1 on the same hour Apple announced it was out, and it was good. I even thought it breathed new life to my aging iPhone 3G that was rendered slow-as-molasses useless with the 3.0 update, although it could just be placebo effect because I have not found any confirmation from the fountain of all knowledge. Not long after, cries from deserts far and wide started pouring in: the new update, when running off Microsoft Exchange 2007 SP1, renders anything but the iPhone 3GS useless for business users. Maybe I should not have been as antsy to upgrade. (Updated on 9/19: in two weeks I have had to restore my iPhone thrice already. There’s a bad bug that wipes out your entire Library on the device when the iTunes app crashes while downloading a song/podcast)

I had a BFO moment: Apple doesn’t get the enterprise, and here’s why I doubt they will anytime soon:

Exhibit #1: Apple discloses very little about its software. The recent 3.1 update for iPhone OS described feature changes to the way the device works, but not a peep that device encryption support for Exchange has changed fundamentally and left people whose lives depended on Exchange, in the washers, so to speak. Prior to 3.1, I have not read information anywhere that Apple’s devices essentially breached Exchange’s device encryption policy and it’s a little insulting that Exchange support has had a happy little section on Apple’s business page since the iPhone 3G was released in 2008.

Exhibit #2: Apple does not encourage predictability. Consider the highly published SMS hijack affecting multiple mobile platforms: after it was identified that the iPhone was also vulnerable, there was no telling when the fix will be made, and more importantly that if it will be fixed at all. iPhone OS 3.0.1 dropped without warning.

Industries have been built around ensuring maximum uptime, risks are identified and mitigation strategies are laid out ahead of time. This would be completely impossible without input on Apple’s part as to what and when known issues will be patched. I cannot wrap my head around the fact that Apple, an enterprise environment of their own with 35,000 employees and 251 locations as of early 2009, speaks out of both sides of its mouth. It’s either feinted naïveté, or that Steve’s Culture of Smug that has reverberated across the entire company has reached the new lows of arrogance.

Exhibit #3: Apple has a track record of abandoning legacy systems and rebooting when it feels like it cannot further that technology. Cases in point: OS 9, PowerPC and iMovie HD; more recently and perhaps more relevant to the subject: the original iPhone, iPhone 3G, and the first two generations of the iPod touch without hardware encryption. For all the wrong decisions that were made in Microsoft’s history, there is something to be said for its stance on legacy support. Case in point: official support for Windows 3.1 ended only two decades (almost) after Microsoft cut off the oxygen late last year.

Exhibit #4: Apple works as if its marketing muscle impresses the enterprise,but this becomes an issue of unmet expectations where there are product feature gaps to be found between its engineering and marketing divisions (refer back to example in Exhibit #1)

To Mr Jobs: iTunes is not an enterprise application, not especially when you suggest that users can spend all of their nine work hours rocking out to Miley Cyrus; see, even Windows Media Player is restricted on desktops of information sweatshop workers.

Exhibit #5: Everything we’ve seen so far just makes it all the more obvious that Apple is half-hearted about the enterprise. Sure, there’s Exchange for iPhone and Snow Leopard, but the forms they take now are not what they had right out of the gate. Certificates, configuration profiles/identities, WPA2 encryption and Cisco IPSec VPN, were only introduced in iPhone OS 2.0, and were further extended to include L2TP, PPTP and on-device encryption only in iPhone OS 3.0 (the latter of which the security community just scoffs at). Apple’s feigned support for Exchange bites it back in the behind and only furthers the argument that the company is completely clueless about the market it’s trying to impress, and that they’ve bit off more than they can chew.

The takeaway here is that while Apple did not need the enterprise to build a successful empire, it understands the financial opportunity the enterprise market represents and realizes that it needs to move into the space to drive even more growth. Apple is clearly testing the waters, but with the mistakes it is making, it is clear that the company is a novice in this space. Enterprise customers tend to not forget easily and it might be better off for Apple to invest some of its 28.1 billion sitting ducks towards research as to how enterprise environments actually operate outside their happy little world.

This whole diatribe because I was this close to (and will soon likely be) unable to use my iPhone to get my work email and calendar. I just hope my sys admin doesn’t find out about the magic checkbox until I can replace my iPhone 3G.

@5 months ago
#Apple #Enterprise 
On why "fixing" iPhone's Exchange support shows that Apple is clueless about the enterprise

I upgraded to iPhone OS 3.1 on the same hour Apple announced it was out, and it was good. I even thought it breathed new life to my aging iPhone 3G that was rendered slow-as-molasses useless with the 3.0 update, although it could just be placebo effect because I have not found any confirmation from the fountain of all knowledge. Not long after, cries from deserts far and wide started pouring in: the new update, when running off Microsoft Exchange 2007 SP1, renders anything but the iPhone 3GS useless for business users. Maybe I should not have been as antsy to upgrade. (Updated on 9/19: in two weeks I have had to restore my iPhone thrice already. There’s a bad bug that wipes out your entire Library on the device when the iTunes app crashes while downloading a song/podcast)

I had a BFO moment: Apple doesn’t get the enterprise, and here’s why I doubt they will anytime soon:

Exhibit #1: Apple discloses very little about its software. The recent 3.1 update for iPhone OS described feature changes to the way the device works, but not a peep that device encryption support for Exchange has changed fundamentally and left people whose lives depended on Exchange, in the washers, so to speak. Prior to 3.1, I have not read information anywhere that Apple’s devices essentially breached Exchange’s device encryption policy and it’s a little insulting that Exchange support has had a happy little section on Apple’s business page since the iPhone 3G was released in 2008.

Exhibit #2: Apple does not encourage predictability. Consider the highly published SMS hijack affecting multiple mobile platforms: after it was identified that the iPhone was also vulnerable, there was no telling when the fix will be made, and more importantly that if it will be fixed at all. iPhone OS 3.0.1 dropped without warning.

Industries have been built around ensuring maximum uptime, risks are identified and mitigation strategies are laid out ahead of time. This would be completely impossible without input on Apple’s part as to what and when known issues will be patched. I cannot wrap my head around the fact that Apple, an enterprise environment of their own with 35,000 employees and 251 locations as of early 2009, speaks out of both sides of its mouth. It’s either feinted naïveté, or that Steve’s Culture of Smug that has reverberated across the entire company has reached the new lows of arrogance.

Exhibit #3: Apple has a track record of abandoning legacy systems and rebooting when it feels like it cannot further that technology. Cases in point: OS 9, PowerPC and iMovie HD; more recently and perhaps more relevant to the subject: the original iPhone, iPhone 3G, and the first two generations of the iPod touch without hardware encryption. For all the wrong decisions that were made in Microsoft’s history, there is something to be said for its stance on legacy support. Case in point: official support for Windows 3.1 ended only two decades (almost) after Microsoft cut off the oxygen late last year.

Exhibit #4: Apple works as if its marketing muscle impresses the enterprise,but this becomes an issue of unmet expectations where there are product feature gaps to be found between its engineering and marketing divisions (refer back to example in Exhibit #1)

To Mr Jobs: iTunes is not an enterprise application, not especially when you suggest that users can spend all of their nine work hours rocking out to Miley Cyrus; see, even Windows Media Player is restricted on desktops of information sweatshop workers.

Exhibit #5: Everything we’ve seen so far just makes it all the more obvious that Apple is half-hearted about the enterprise. Sure, there’s Exchange for iPhone and Snow Leopard, but the forms they take now are not what they had right out of the gate. Certificates, configuration profiles/identities, WPA2 encryption and Cisco IPSec VPN, were only introduced in iPhone OS 2.0, and were further extended to include L2TP, PPTP and on-device encryption only in iPhone OS 3.0 (the latter of which the security community just scoffs at). Apple’s feigned support for Exchange bites it back in the behind and only furthers the argument that the company is completely clueless about the market it’s trying to impress, and that they’ve bit off more than they can chew.

The takeaway here is that while Apple did not need the enterprise to build a successful empire, it understands the financial opportunity the enterprise market represents and realizes that it needs to move into the space to drive even more growth. Apple is clearly testing the waters, but with the mistakes it is making, it is clear that the company is a novice in this space. Enterprise customers tend to not forget easily and it might be better off for Apple to invest some of its 28.1 billion sitting ducks towards research as to how enterprise environments actually operate outside their happy little world.

This whole diatribe because I was this close to (and will soon likely be) unable to use my iPhone to get my work email and calendar. I just hope my sys admin doesn’t find out about the magic checkbox until I can replace my iPhone 3G.

5 months ago
#Apple #Enterprise